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Aisha Khan
Another approach worth considering - have you looked into setting up a Section 105 Plan? It's specifically designed for situations like yours. I'm a solo founder of a C Corp too, and my accountant helped me set this up. A Section 105 Plan allows your C Corp to reimburse you for medical expenses, including health insurance premiums. The reimbursements are tax-deductible to the corporation and tax-free to you. You'll need proper documentation, but it can be a great solution for solo C Corp owners.
Diego Vargas
ā¢I've never heard of a Section 105 Plan before. Is this something I need to set up before paying the premiums, or can it be established retroactively for premiums I've already paid out of pocket?
Aisha Khan
ā¢Ideally, you want to set up the Section 105 Plan before paying premiums. However, if you've already paid premiums personally, the plan can be established at any time during the tax year. Just make sure the plan documents are properly created and signed before December 31. After setting up the plan, your corporation can reimburse you for the premiums you paid personally. The reimbursement is deductible to the company and not taxable to you. Just be sure to keep excellent records of both the plan documentation and the reimbursements to satisfy any potential IRS questions.
Ethan Taylor
Something critical that nobody's mentioned yet - as a C Corp with no revenue, you need to be careful about potential hobby loss rules. If you're not showing legitimate business activity, the IRS might question whether this is actually a business. Make sure you're documenting all your startup activities, have a solid business plan, and are making efforts to generate revenue. This will protect both your business deductions and any health insurance arrangements you set up.
Yuki Ito
ā¢I don't think hobby loss rules apply to C Corporations though? I thought that was just for individuals filing Schedule C or partnerships?
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Something nobody's mentioned yet - if your LLC is taxed as an S-Corporation, there's another wrinkle to consider. You need to be really careful about how you document any money moving from personal to business accounts to avoid it looking like constructive dividends going the wrong way. My accountant always advises setting up a clear paper trail showing the funds as either 1) additional paid-in capital or 2) a formal loan to the business with proper documentation. Just randomly moving money between accounts without documentation is asking for trouble if you're ever audited.
What kind of documentation would you need for the loan option? Is a simple promissary note enough or does it need to be more formal?
For a loan to your business, you need more than just a promissory note, though that's a good start. You should have a formal loan agreement that includes the principal amount, interest rate (should be at or above the applicable federal rate), repayment schedule, and consequences of default. Both parties should sign and date it. You also need to treat it like a real loan - make the scheduled payments, record the interest properly, and have your business actually pay you back according to the terms. If you don't follow through with actual repayments, the IRS could reclassify it as a capital contribution or income.
Kai Santiago
Just FYI - no matter how you structure moving the money from personal to business accounts, you're still gonna pay the same taxes on your stock gains. The only difference is whether you'll have proper documentation for the business side of things. And don't forget that different tax rates apply to stock gains depending on how long you held them! If you held the stocks for more than a year, those are long-term capital gains with lower tax rates. If less than a year, they're short-term gains taxed at your ordinary income rate.
Lim Wong
ā¢This is the key point - the stock profits are taxed the same either way. What you're really asking about is the best way to get money into your business for equipment purchases, not how to reduce taxes on your stock gains.
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For your AI tool, don't forget about administrative materials beyond just the tax code. A huge part of my research involves Treasury regulations, Revenue Rulings, Revenue Procedures, Private Letter Rulings, Technical Advice Memoranda, and Chief Counsel Advice. Court cases are also crucial since judicial interpretations can dramatically affect how tax laws are applied. These aren't always easy to find in one place, which makes research time-consuming.
Do you have any recommendations for keeping track of all these different sources? I'm a new CPA and finding it overwhelming to organize everything.
I use a combination of methods. For larger clients with recurring issues, I maintain dedicated folders organized by topic rather than by client, which helps when similar issues come up with different clients. I also keep a personal knowledge base with notes on important rulings and interpretations. For research organization, I've found that creating summary documents with hyperlinks to primary sources works better than trying to save everything. Focus on understanding the principles and knowing where to find the details when you need them, rather than memorizing everything.
Ev Luca
Don't forget about state tax resources! I specialize in multi-state taxation and it's a nightmare keeping up with 50+ different jurisdictions. The Federation of Tax Administrators website has links to all state tax departments. Also, many states have taxpayer advocate services that can provide guidance on complex state-specific issues.
Avery Davis
ā¢State tax compliance is the bane of my existence! Do you use any specific tools for state tax research?
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Back to the original question - there are legitimate ways people end up with 1099-Cs that aren't sketchy. I've had clients get them from: 1. Mortgage debt forgiveness on underwater homes 2. Credit card settlements (pay $5K on a $15K balance, get a 1099-C for $10K) 3. Business loans that failed and eventually got written off 4. Medical debt that went to collections and was settled 5. Car repos where they owed more than the car was worth Most people don't plan to get a 1099-C - it usually comes after financial hardship. Your clients may be doing well now, but could have had past issues.
Mia Green
ā¢Is it possible to deliberately seek debt cancellation as a strategy? I have clients asking about this as if it's a financial hack.
You can strategically settle debts for less than you owe, knowing you'll get a 1099-C, but it's not the "free money" hack people think it is. Here's why: First, you'll pay income tax on the forgiven amount - often 22-24% for most people. Second, your credit score takes a massive hit that can last 7+ years, affecting everything from mortgage rates to insurance premiums. Third, you generally need to be significantly behind on payments before creditors will settle, which means months or years of collection calls, potential lawsuits, and stress. Some clients come in thinking debt settlement is a clever financial strategy, but for most people, the long-term costs outweigh the benefits. The clients who come out ahead usually had legitimate hardships and no real ability to pay the original debt, so the tax hit is better than bankruptcy.
Emma Bianchi
I had this EXACT situation with a client last month. Made nearly $200k but had three 1099-Cs totaling over $40k. Turns out they had invested in a restaurant franchise that failed during covid. The business took out loans, and when it went under, the loans eventually got written off but my client was a personal guarantor. They're doing well financially now, but that failed business venture is still causing tax headaches. It's usually not the currently wealthy trying to game the system - it's people who had legitimate financial troubles in the past and are recovering.
Would the Qualified Principal Residence Indebtedness exclusion apply to business debts like that? Or just primary residence mortgages?
Mei Wong
Have you tried Credit Karma Tax? It's completely free for all forms and I found it actually gave me a slightly better refund than TurboTax free did when I tried both last year. Worth checking out as another option.
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Mateo Lopez
ā¢I haven't tried Credit Karma Tax yet. Is it really completely free even for state returns? No hidden charges or upgrade prompts halfway through?
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Mei Wong
ā¢Yes, it's completely free for both federal and state returns. I used it last year and didn't encounter any upgrade prompts or hidden fees at all. They offer all the major forms and schedules at no cost. It's now called Cash App Taxes (Credit Karma sold that part of their business), but it's still free. The interface isn't quite as polished as TurboTax, but it works well and covers most tax situations including self-employment, investments, and homeowner deductions without charging anything.
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Liam Fitzgerald
Your refund is probably tiny because your withholding was more accurate this year, meaning you got more money in each paycheck instead of giving the IRS an interest-free loan. A smaller refund can actually be a good thing! Check your W2 box 2 and compare it to last year to see if you had less federal tax withheld.
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PixelWarrior
ā¢This is the correct answer. People think big refund = good, small refund = bad, but that's backward. Ideally you want your refund to be as close to $0 as possible, meaning you paid exactly what you owed throughout the year.
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